WO2014003405A1 - Nouveau composé et dispositif émettant de la lumière le comprenant - Google Patents

Nouveau composé et dispositif émettant de la lumière le comprenant Download PDF

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WO2014003405A1
WO2014003405A1 PCT/KR2013/005588 KR2013005588W WO2014003405A1 WO 2014003405 A1 WO2014003405 A1 WO 2014003405A1 KR 2013005588 W KR2013005588 W KR 2013005588W WO 2014003405 A1 WO2014003405 A1 WO 2014003405A1
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group
light emitting
emitting device
compound
halogen
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PCT/KR2013/005588
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Korean (ko)
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이준혁
함호완
안현철
김동준
한정우
김근태
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주식회사 제이앤드제이 캐미칼
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Priority claimed from KR1020130072449A external-priority patent/KR102191154B1/ko
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Publication of WO2014003405A1 publication Critical patent/WO2014003405A1/fr

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Definitions

  • the present invention relates to a novel compound and a light emitting device comprising the same.
  • an organic light emitting device capable of low voltage driving with a self-luminous type has a superior viewing angle, contrast ratio, and the like, and is lighter and thinner than a liquid crystal display (LCD), which is the mainstream of flat panel display devices.
  • LCD liquid crystal display
  • the organic light emitting device has a structure including a cathode (electron injection electrode) and an anode (hole injection electrode), and an organic layer between the two electrodes.
  • the organic layer may include a hole injection layer (HIL), a hole transport layer (HTL), an electron transport layer (ETL), or an electron injection layer (EIL) in addition to the light emitting layer (EML).
  • an electron injection layer and may further include an electron blocking layer (EBL) or a hole blocking layer (HBL) due to the light emission characteristics of the light emitting layer.
  • a light emitting dye may be doped into the light emitting layer (host).
  • HOLEDs hybrid organic-inorganic light emitting devices
  • an electron injection layer or an electron transport layer is formed of an n-type semiconductor metal oxide to improve electroluminescence efficiency and brightness.
  • Korean Patent Publication No. 10-2011-0132165 discloses a HOLED having improved performance by modifying the n-type semiconductor metal oxide of the HOLED with a self-assembled dipole molecule having a specific chemical formula, but the production productivity and performance of the HOLED are still present. There is a great demand for improvement.
  • the present invention has excellent electron transfer characteristics, excellent driving voltage, high luminous efficiency and luminous luminance, long life can be realized, as well as a compound that can significantly improve the manufacturing productivity, including the same It is an object to provide a light emitting element.
  • A is deuterium, halogen, amino group, nitrile group, nitro group, substituted or unsubstituted C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 1 to C 40 alkoxy group, C 3 to C 40 Fluorescence or phosphorescence unsubstituted or substituted with one or more groups selected from the group consisting of a cycloalkyl group, C 3 -C 40 heterocycloalkyl group, C 6 -C 40 aryl group, C 3 -C 40 heteroaryl group and Si Compound;
  • R a is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group, C 3 ⁇ C 40 heteroaryl group, and is optionally substituted with one or more groups selected from the group consisting of Si C alkyl group of 1 ⁇ C 40 of the ; C 3 -C 40 cycloalkyl group; C 3 ⁇ C 40 alkenyl group; C 3 ⁇ C 40 Alkoxy group; Amino group; C 6 -C 40 aryl group; C 3 ⁇ C 40 heteroaryl group; Or Si, wherein adjacent rings may be fused to each other;
  • R b is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group, C 3 ⁇ C 40 heteroaryl group, and is optionally substituted with one or more groups selected from the group consisting of Si C alkyl group of 1 ⁇ C 40 of the ; C 3 -C 40 cycloalkyl group; C 3 ⁇ C 40 alkenyl group; C 3 ⁇ C 40 Alkoxy group; Amino group; C 6 -C 40 aryl group; C 3 ⁇ C 40 heteroaryl group; Or Si, wherein adjacent rings may be fused to each other;
  • D is one of those represented by the following formulas Fg1 to Fg25, where * is a linking moiety, and R f1 to Rf 10 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; Or a substituted or unsubstituted C 1 -C 40 alkyl group substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group; C 3 -C 40 cycloalkyl group; C 3 ⁇ C 40 alkenyl group; C 3 ⁇ C 40 Alkoxy group; C 6 -C 40 aryl group; C 3 ⁇ C 40 heteroaryl group; Or Si, and Rw is each independently a substituted or unsubstituted C 1 -C 40 alkyl group substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group; C 3 -C 40 cycloalkyl group; C 3 ⁇ C
  • n and m are each independently an integer of 0 to 10,
  • p is an integer from 1 to 10:
  • the present invention provides a method for preparing a compound represented by the formula (1).
  • the present invention provides a light emitting device comprising a compound represented by the formula (1).
  • the present invention provides a method for manufacturing a light emitting device, characterized in that using the compound represented by the formula (1).
  • the compound of formula 1 according to the present invention induces the formation of covalent bonds on the surface of the metal oxide to enrich the electrons on the surface of the metal oxide to increase the Fermi level (fermi level) electrons injected from the cathode during the formation of the light emitting device to the metal oxide
  • the energy barrier can be lowered in moving to the light emitting layer.
  • the compound of the present invention when the compound of the present invention is applied to the light emitting device, electrons can be easily moved between the metal oxide interface and the organic material layer, and the driving voltage, light emitting efficiency and lifespan characteristics of the light emitting device can be remarkably improved, and the application to the light emitting device It is possible to greatly improve the manufacturing productivity of the light emitting device by enabling the wet process process in the.
  • FIG. 1 is a schematic diagram schematically showing the structure of an organic light emitting device according to an embodiment of the present invention.
  • I-V-L current density-voltage-luminance
  • 3 is a graph showing the efficiency characteristics of the organic light emitting device according to an embodiment of the present invention.
  • Compound of the present invention represented by the following formula (1) is characterized in that the fluorescent or phosphorescent compound is substituted with an electron-rich functional group to form a dipole moment.
  • A is deuterium, halogen, amino group, nitrile group, nitro group, substituted or unsubstituted C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 1 to C 40 alkoxy group, C 3 to C 40 a cycloalkyl group, C 3 ⁇ C 40 of the heterocycloalkyl group, C 6 ⁇ C 40 aryl group and C 3 ⁇ C 40 heteroaryl group is a fluorescent or phosphorescent compound is optionally substituted with one or more groups selected from the group consisting of;
  • R a is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group and C 3 ⁇ C 40 heteroaryl group that is optionally substituted with one or more groups selected from the group consisting of C 1 ⁇ C 40 alkyl group of; C 3 -C 40 cycloalkyl group; C 3 ⁇ C 40 alkenyl group; C 3 ⁇ C 40 Alkoxy group; Amino group; C 6 -C 40 aryl group; C 3 ⁇ C 40 heteroaryl group; Or Si, wherein adjacent rings may be fused to each other;
  • R b is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 3 ⁇ C 40 cycloalkyl group, C 3 ⁇ C 40 heterocycloalkyl group, C 6 ⁇ C 40 aryl group and C 3 ⁇ C 40 heteroaryl group that is optionally substituted with one or more groups selected from the group consisting of C 1 ⁇ C 40 alkyl group of; C 3 -C 40 cycloalkyl group; C 3 ⁇ C 40 alkenyl group; C 3 ⁇ C 40 Alkoxy group; Amino group; C 6 -C 40 aryl group; C 3 ⁇ C 40 heteroaryl group; Or Si, wherein adjacent rings may be fused to each other;
  • D is one of those represented by the following formulas Fg1 to Fg25, where * is a linking moiety, and R f1 to Rf 10 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; Or a substituted or unsubstituted C 1 -C 40 alkyl group substituted with deuterium, a halogen, an amino group, a nitrile group, a nitro group; C 3 -C 40 cycloalkyl group; C 3 ⁇ C 40 alkenyl group; C 3 ⁇ C 40 Alkoxy group; C 6 -C 40 aryl group; C 3 ⁇ C 40 heteroaryl group; Si is each independently Rw is a substituted or unsubstituted C 1 ⁇ C 40 alkyl group substituted with deuterium, halogen, amino, nitrile, nitro group; C 3 -C 40 cycloalkyl group; C 3 ⁇ C 40 alkenyl group; C 3 ⁇
  • n and m are each independently an integer of 0 to 10,
  • p is an integer from 1 to 10:
  • the fluorescent or phosphorescent compound may be a known fluorescent or phosphorescent compound used as a conventional fluorescent or phosphorescent compound.
  • the fluorescent or phosphorescent compound may be a fluorescent compound represented by the following FL1 to FL33 or a phosphorescent compound represented by PL1 to PL59, and in FL1 to FL33, or PL1 to PL59, * is a connecting portion, wherein the connecting portion is It may be connected to one or more of the substitution positions in parentheses,
  • R1 to R16 are each independently hydrogen; heavy hydrogen; halogen; Amino group; Nitrile group; Nitro group; C 1 -C 40 alkyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2 -C 40 alkenyl group; C 1 ⁇ C 40 Alkoxy group; C 3 -C 40 cycloalkyl group; C 3 ⁇ C 40 Heterocycloalkyl group; C 6 -C 40 aryl group; C 3 ⁇ C 40 heteroaryl group; Or Si.
  • both n and m of R a and R b may be 0, n and m are each independently an integer of 0 to 10, and R a or R b are specific examples. It may be a compound as follows.
  • * represents a linking moiety, at least one hydrogen other than the linking part is deuterium; halogen; Amino group; Nitrile group; Nitro group; C 1 -C 40 alkyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2 -C 40 alkenyl group; C 1 ⁇ C 40 Alkoxy group; C 3 -C 40 cycloalkyl group; C 3 ⁇ C 40 Heterocycloalkyl group; C 6 -C 40 aryl group; It may be substituted with one or more groups selected from the group consisting of C 3 ⁇ C 40 heteroaryl group and Si.
  • R is each independently a C 1 ⁇ C 40 alkyl group which is unsubstituted or substituted with deuterium, halogen, amino group, nitrile group, nitro group; C 2 -C 40 alkenyl group; C 1 ⁇ C 40 Alkoxy group; C 3 -C 40 cycloalkyl group; C 3 ⁇ C 40 Heterocycloalkyl group; C 6 -C 40 aryl group; C is a heteroaryl group of 3 ⁇ C 40.
  • the compound of formula 1 of the present invention may be a compound in which A, Ra, Rb, and D are bound through any combination according to the values of n, m, and p, and when n and m are both 0, A and D May be combined directly. More specifically, the compound of Formula 1 of the present invention may be any one of the compounds represented by Table 1 below. In Table 1 below, A, Ra, Rb, and D are as defined above.
  • the compound represented by Formula 1 of the present invention may be one of the following compounds.
  • the compound of formula 1 according to the present invention forms a dipole moment, thereby inducing covalent bond formation on the surface of the metal oxide to enrich the electrons on the surface of the metal oxide. Therefore, by increasing the Fermi level (fermi level) it is possible to lower the energy barrier for electrons injected from the cathode to move to the light emitting layer through the metal oxide when forming the light emitting device.
  • Fermi level Fermi level
  • the compound of the present invention when the compound of the present invention is applied to a light emitting device such as a HOLED or an OLED, electrons can be easily moved between the metal oxide interface and the organic material layer, and the characteristics such as driving voltage and luminous efficiency of the light emitting device can be improved.
  • the wet process process can be enabled, thereby significantly improving the production productivity of the light emitting device.
  • the compound of formula 1 according to the present invention may be prepared by binding D to compound AX, A-Ra-X, or A-Ra-Rb-X.
  • A, Ra, Rb, and D are as defined in Formula 1
  • X is a halogen compound.
  • the compound of Formula 1 according to the present invention may be prepared through any one of the following schemes.
  • Chemical Formula 1 according to the present invention may be prepared through the process described below.
  • the present invention also provides a light emitting device comprising the compound represented by Formula 1 as a light emitting material.
  • the light emitting device may be a HOLED or an OLED light emitting device.
  • the compound may be included in the light emitting layer of the light emitting device, wherein the compound of the present invention may be used alone or in combination with a known organic light emitting compound.
  • the light emitting device of the present invention is a HOLED light emitting device
  • the light emitting device may include an n-type metal oxide in the electron injection or electron transport layer.
  • the n-type metal oxide may be formed using a metal oxide such as ZnO, TiO 2 , ZrO 2 , Ta 2 O 3 , MgO, or HfO 2 .
  • the light emitting device may further include a hole transport and a hole transport layer between the electrode and the light emitting layer, and the hole transport and hole transport layer may be formed of a P-type metal oxide or an organic material layer.
  • the present invention provides a method of manufacturing a light emitting device comprising the compound represented by the formula (1).
  • a light emitting device comprising the compound represented by the formula (1).
  • well-known methods used in the manufacturing method of a known light emitting device may be applied. It may be a HOLED or OLED device, it may include a compound of Formula 1 of the present invention in the light emitting layer.
  • the HOLED light emitting device may apply the method described in Korean Patent Publication No. 10-2011-0132165, except that the compound of Formula 1 is used as a light emitting compound, and an electron injection and electron transport layer formed of n-type metal oxide. It is also possible to form a light emitting layer directly thereon.
  • the light emitting device of the present invention may be an OLED light emitting device, and the OLED compound through the method described in Korean Patent Application No. 10-2009-30213 of the present applicant, except that the compound of Formula 1 is used as a light emitting compound It may also be prepared.
  • the method of manufacturing the light emitting device of the present invention in the formation of the light emitting layer, it is possible to form a light emitting layer through a wet process using the compound of the formula (1) can significantly improve the manufacturing productivity of the light emitting device, luminous efficiency, brightness and light emission There is an advantage that can improve the life of the device.
  • Example 1 Preparation of Example 1 except for reacting with 4'-bromo-N, N-diphenyl- [1,1'-biphenyl] -4-amine in place of 9- (4-bromophenyl) -10-phenylanthracene
  • the following compound was prepared using the same method as the method.
  • Example 6 The same method as in Example 6 was used except that 9-bromo-10-phenylanthracene was reacted with N9- (4-bromophenyl) -N9, N10, N10-triphenylanthracene-9,10-diamine. The following compound was prepared.
  • an organic light emitting device having a structure as shown in FIG. Specifically, it is as follows.
  • a glass substrate coated with an indium tin oxide (ITO) 1500 ⁇ thick thin film was washed by distilled water ultrasonically. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc., dried, transferred to a plasma cleaner, and then cleaned the substrate using oxygen plasma for 5 minutes, and then zinc oxide as an electron transfer layer on the top of the ITO substrate.
  • a film thickness of 85 nm was formed by spin coating nanoparticles (ZnO nanoparticles).
  • the compound synthesized in Examples 1 to 16 was dissolved in chlorobenzene to prepare a 1 wt% solution, and 100 nm was formed into a light emitting layer by spin coating.
  • PVK was dissolved in chlorobenzene to prepare a 1 wt% solution, and 50 nm was formed into a hole transport layer by spin coating.
  • a reverse structure organic light emitting device was fabricated by using a vacuum deposition apparatus to form MoO 3 as a hole injection layer at 10 nm and an anode as Al at 100 nm, and sealing the device in a glove box.
  • the device characteristics of the organic light emitting device was measured.
  • the organic light emitting device manufactured using the compound of Example 11 exhibited excellent current density-voltage-luminance (IVL) characteristics and efficiency as shown in FIGS. 2 and 3 when measured with a Keithley-236 source-measurement unit.
  • IVL current density-voltage-luminance
  • the organic light emitting device using 1 to 10 and the compounds 12 to 16, but also not attached to the drawings it showed good luminance and luminous efficiency as in Example 11.
  • the compound of formula 1 according to the present invention induces the formation of covalent bonds on the surface of the metal oxide to enrich the electrons on the surface of the metal oxide to increase the Fermi level (fermi level) electrons injected from the cathode during the formation of the light emitting device to the metal oxide
  • the energy barrier can be lowered in moving to the light emitting layer.
  • the compound of the present invention when the compound of the present invention is applied to the light emitting device, electrons can be easily moved between the metal oxide interface and the organic material layer, and the driving voltage, light emitting efficiency and lifespan characteristics of the light emitting device can be remarkably improved, and the application to the light emitting device It is possible to greatly improve the manufacturing productivity of the light emitting device by enabling the wet process process in the.

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Abstract

La présente invention concerne un nouveau composé et un dispositif émettant de la lumière le comprenant. Le composé de la présente invention présente d'excellentes caractéristiques de transport d'électrons et peut donc être utilisé comme matériau lumineux, destiné à un dispositif émettant de la lumière, pour améliorer la tension d'attaque, l'efficacité lumineuse et les caractéristiques de durée de vie du dispositif émettant de la lumière, et augmente considérablement la productivité de la fabrication.
PCT/KR2013/005588 2012-06-26 2013-06-25 Nouveau composé et dispositif émettant de la lumière le comprenant WO2014003405A1 (fr)

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CN106867522A (zh) * 2017-04-01 2017-06-20 武汉大学 氰基乙酸的新用途
CN110229055A (zh) * 2019-05-31 2019-09-13 苏州科技大学 具有宽光谱上转换白光发射特性的蒽衍生物及弱光上转换白光体系
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US11066394B2 (en) 2019-08-06 2021-07-20 Incyte Corporation Solid forms of an HPK1 inhibitor
US11111247B2 (en) 2018-09-25 2021-09-07 Incyte Corporation Pyrazolopyrimidine compounds and uses thereof
WO2021210304A1 (fr) * 2020-04-15 2021-10-21 出光興産株式会社 Composé, élément électroluminescent organique et dispositif électronique
CN113583156A (zh) * 2021-06-30 2021-11-02 苏州大学 用于高通量太阳光敞口聚合的孔板制备方法及高通量太阳光敞口聚合方法
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US11242343B2 (en) 2016-09-09 2022-02-08 Incyte Corporation Pyrazolopyridine compounds and uses thereof
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US10722495B2 (en) 2017-09-08 2020-07-28 Incyte Corporation Cyanoindazole compounds and uses thereof
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US10745388B2 (en) 2018-02-20 2020-08-18 Incyte Corporation Indazole compounds and uses thereof
US11731958B2 (en) 2018-02-20 2023-08-22 Incyte Corporation Carboxamide compounds and uses thereof
US10752635B2 (en) 2018-02-20 2020-08-25 Incyte Corporation Indazole compounds and uses thereof
US10800761B2 (en) 2018-02-20 2020-10-13 Incyte Corporation Carboxamide compounds and uses thereof
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US10899755B2 (en) 2018-08-08 2021-01-26 Incyte Corporation Benzothiazole compounds and uses thereof
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CN110229055B (zh) * 2019-05-31 2021-12-28 苏州科技大学 具有宽光谱上转换白光发射特性的蒽衍生物及弱光上转换白光体系
CN110229055A (zh) * 2019-05-31 2019-09-13 苏州科技大学 具有宽光谱上转换白光发射特性的蒽衍生物及弱光上转换白光体系
US11066394B2 (en) 2019-08-06 2021-07-20 Incyte Corporation Solid forms of an HPK1 inhibitor
US11787784B2 (en) 2019-08-06 2023-10-17 Incyte Corporation Solid forms of an HPK1 inhibitor
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JP7546046B2 (ja) 2020-04-15 2024-09-05 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子及び電子機器
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